Carbon Tetrachloride → HCID 22154346, compound

HRID 1053688Notes

Reaction equation

HRID 1053688 reaction equation
FF.[C:3]([Cl:7])([Cl:6])([Cl:5])[Cl:4].[C:8]1([P:14]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>ClCCl>[C:21]1([P:14]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1.[Cl:4][C:3]([Cl:7])([Cl:6])[Cl:5]

Participants

5

Reactant 3

HCID 5943Carbon Tetrachloride2×HCID 11776TriphenylphosphineHCID 24524Fluorine

Product 1

HCID 22154346HCID 22154346, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Adapting literature known protocols (Buss, et al., J. Fluorine Chem., 1986, 34(1), 83-114; and Kupczyk-Subotkowska, et al., J. Drug Targeting, 1997, 4(6), 359-370), a solution of the corresponding N,N-bis(2-hydroxyethyl) derivative (5 mmol) in anhydrous dichloromethane (DCM) (about 25 mL) containing carbon tetrachloride (CCl4) (15-25 mmol) is cooled to about 0° C. (ice bath). Alternatively, neat carbon tetrachloride (CCl4) (25 mL) is used as a reaction solvent. The reaction mixture is stirred, and triphenylphosphine (Ph3P) (10-15 mmol) is added in portions. The reaction mixture is stirred for about 8-14 h with gradual warming to room temperature. Alternatively, the reaction mixture is heated at reflux for about 2-6 h. The reaction course is followed by TLC and/or LC/MS till completion. The reaction mixture is cooled to room temperature and the solvents are removed under reduced pressure using a rotary evaporator. The residue is triturated with diethyl ether (Et2O) (3×) to remove some of the triphenylphosphine oxide (Ph3PO). The organic phase is evaporated under reduced pressure using a rotary evaporator. The remainder of the reaction, work-up, and product isolation are conducted as described in Variant A.

Workup

  1. stirringThe reaction mixture is stirred for about 8-14 h
  2. temperaturewith gradual warming to room temperature
  3. temperatureAlternatively, the reaction mixture is heated
  4. temperatureat reflux for about 2-6 h
  5. temperatureThe reaction mixture is cooled to room temperature
  6. customthe solvents are removed under reduced pressure
  7. customa rotary evaporator
  8. customThe residue is triturated with diethyl ether (Et2O) (3×)
  9. customto remove some of the triphenylphosphine oxide (Ph3PO)
  10. customThe organic phase is evaporated under reduced pressure
  11. customa rotary evaporator
  12. customThe remainder of the reaction

Sources & evidence

ORD record
ord-75046e944690463a90750b2dc2298115
Source dataset
uspto-grants-2016_07
Patent number
US09394236B2

Reaction notes

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